(6-Cyclopentyloxy-pyridin-3-yl)-carbamic acid 4-nitro-phenyl ester → 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid (6-cyclopentyloxy-pyridin-3-yl)-amide

HRID 657248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657248
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[N+](C1C=CC([O:30][C:31](=O)[NH:32][C:33]2[CH:34]=[N:35][C:36]([O:39][CH:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:37][CH:38]=2)=CC=1)([O-])=O>C(Cl)Cl>[CH:40]1([O:39][C:36]2[N:35]=[CH:34][C:33]([NH:32][C:31]([N:18]3[CH2:19][CH2:20][CH:15]([C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][N:7]=4)[CH2:16][CH2:17]3)=[O:30])=[CH:38][CH:37]=2)[CH2:41][CH2:42][CH2:43][CH2:44]1

Komponenten

4

Edukt 2

HCID 58770029(6-Cyclopentyloxy-pyridin-3-yl)-carbamic acid 4-nitro-phenyl esterHCID 595517346,7-Dimethoxy-4-(piperidin-4-yl)quinazoline

Produkt 1

HCID 587707204-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid (6-cyclopentyloxy-pyridin-3-yl)-amideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 6,7-dimethoxy-4-piperidin-4-yl-quinazoline (12 mg, 0.044 mmol), prepared as described in Example 1d, (6-cyclopentyloxy-pyridin-3-yl)-carbamic acid 4-nitro-phenyl ester (20 mg, 0.058 mmol), prepared as described in the previous step, and DCM (500 uL) was treated with TEA (6 uL, 0.043 mmol) in one portion at rt. The homogeneous amber solution was stirred at rt for 2 h, diluted with DCM (2 mL), and washed with H2O (2 mL). The aqueous layer was extracted with DCM (2×2 mL), the organic layers were combined, dried (Na2SO4) and concentrated in vacuo. Purification by prep tlc (1:9 MeOH/DCM) afforded the title compound (6.0 mg, 29%). 1H-NMR (300 MHz, CDCl3): δ 9.10 (s, 1H), 8.08 (s, 1H), 7.89 (d, 1H), 7.39 (s, 1H), 7.28 (s, 1H), 6.71 (d, 1H), 6.61 (bs, 1H), 5.30 (m, 1H), 4.32 (d, 2H), 4.08 (s, 6H), 3.62 (m, 1H), 3.20 (m, 2H), 2.16 (m, 2H), 1.98 (m, 4H), 1.79 (m, 4H), 1.62 (m, 2H). LC/MS (ESI) calcd for C26H31N5O4 477.56, found [M+1]+ 478.1.

Aufarbeitung

  1. customprepared
  2. customprepared
  3. washwashed with H2O (2 mL)
  4. extractionThe aqueous layer was extracted with DCM (2×2 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by prep tlc (1:9 MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-cea777b775994be18d3fff16c3d26d85
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071768B2

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